Siesta Key, FL Homes

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  /31

  $995,000

  • 2 Beds
  • 2 Baths
  • 1,122 Sq Ft

  757 Beach Rd Unit 310, Sarasota, FL 34242

  Front row view of the world-renowned Siesta Key Beach. This unit is situated right across from the public beach and is withing 0.9 miles/3 minutes to the village. This turnkey fully furnished and equipped unit is move in ready. Right thru the front door you are greeted with an open floor plan overlooking the beach and the gulf water views. Smell the salt air as you lounge or dine on your large

  Shirley LaGrange COLDWELL BANKER REALTY

  757 Beach Rd Unit 310, Sarasota, FL 34242
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  /56

  $5,250 per month

  • 3 Beds
  • 2 Baths
  • 1,822 Sq Ft
  • House for Rent

  726 Birdsong Ln, Sarasota, FL 34242

  AVAILABLE October, November 2025! Currently booked through September 2025. Also booked December - March 2026. WOW! Enjoy a little slice of heaven on the World Famous Siesta Key! This beautifully renovated turnkey 3 bedroom 2 bath, heated pool home, is just a short distance to the #1 rated beaches and the quaint shops and restaurants in the downtown village. Whether it’s our million-dollar

  Scott Nold TNG PROPERTY MANAGEMENT

  726 Birdsong Ln, Sarasota, FL 34242
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  /2

  $2,875,000 Sold Oct 24, 2025

  5169 Sandy Shore Ave, Sarasota, FL 34242

  • 3 Beds
  • 3.5 Baths
  • 2,885 Sq Ft
  • Built 2015

  Last Sold Summary

  • 18% Below List Price
  • $997/SF
  • 219 Days On Market

  Last Listing Agent Andy Barnhardt WATERSIDE REALTY LLC

  5169 Sandy Shore Ave, Sarasota, FL 34242
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  /2

  Est $3,263,354 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 3,759 Sq Ft

  5310 Avenida Del Mare, Siesta Key, FL 34242

  5310 Avenida Del Mare, Siesta Key, FL 34242
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  /37

  $2,500,000

  • 4 Beds
  • 3.5 Baths
  • 3,250 Sq Ft

  1248 Northport Dr, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. Siesta Key, island living at its best. Welcome to your waterside home where you’ll enjoy a carefree, tropical lifestyle all year long. This home has been nicely maintained along with an extensive addition completed in 2015. The original home included two guest bedrooms with adjoining Jack and Jill bath plus a primary suite. The 1,200-square-foot

  Peg Davant PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1248 Northport Dr, Sarasota, FL 34242
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  /45

  $9,500 per month

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Condo for Rent

  1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242

  Welcome to this beautifully designed 2-bedroom, 2-bathroom first floor condo located in the sought-after Gulf and Bayside Bay Club, offers breathtaking views of the boat harbor and Intracoastal Waterway.The kitchen is a chef's delight, boasting stainless steel appliances and sleek countertops. The living room is the perfect place to kick back and relax after a day of adventure, with

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242
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  /2

  $1,400,000 Sold Jul 28, 2025

  309 Avenida Milano, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,439 Sq Ft
  • Built 1974

  Last Sold Summary

  • $973/SF
  • 64 Days On Market

  Current Estimated Value $1,323,636

  Last Listing Agent Tim Yocum, Sr COLDWELL BANKER REALTY

  309 Avenida Milano, Sarasota, FL 34242
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  /83

  Est $608,506 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,271 Sq Ft

  101 Whispering Sands Dr Unit 203, Sarasota, FL 34242

  101 Whispering Sands Dr Unit 203, Sarasota, FL 34242
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  /34

  $2,240,000

  • 3 Beds
  • 2.5 Baths
  • 1,670 Sq Ft

  462 Island Cir, Sarasota, FL 34242

  Beaches, Boating & Bistros. This 3 bedroom, 3 bathroom home has it all. Beaches: Located on Palm Island, an Island on an Island only a 2-minute walk to the world-famous cool quartz sands of Siesta Beach (Beach Access #10). You can walk for miles along the sparkling Gulf waters and watch the dolphins play. Kick back on the white sand, go swimming in the clear water, or simply admire the sunset —

  Dan Miller PREFERRED SHORE LLC

  462 Island Cir, Sarasota, FL 34242
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  /50

  $8,000 per month

  • 2 Beds
  • 2 Baths
  • 1,645 Sq Ft
  • Condo for Rent

  1315 Siesta Bayside Dr Unit 1315B, Sarasota, FL 34242

  Welcome to this stunning 2-bedroom, 2-bathroom lakefront condo located on the second floor in Gulf and Bay Bayside, Siesta Key. This two-story retreat features two primary bedrooms, each with a luxurious king-size bed, spacious walk-in closets, and beautifully appointed bathrooms with walk-in showers. In the second floor primary bedroom there is additional sleeping accommodations with a full-size

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1315 Siesta Bayside Dr Unit 1315B, Sarasota, FL 34242
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  /2

  $975,000 Sold Dec 09, 2025

  568 Venice Ln, Sarasota, FL 34242

  • 3 Beds
  • 3 Baths
  • 1,818 Sq Ft
  • Built 1975

  Last Sold Summary

  • 13% Below List Price
  • $536/SF
  • 141 Days On Market

  Last Listing Agent Wade Stafford ALL FLORIDA PROPERTY GROUP,INC

  568 Venice Ln, Sarasota, FL 34242
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  /37

  Est $562,473 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft

  1300 Cove II Place Unit 731, Sarasota, FL 34242

  1300 Cove II Place Unit 731, Sarasota, FL 34242
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  /45

  $1,277,000

  • 2 Beds
  • 2 Baths
  • 1,285 Sq Ft

  5830 Midnight Pass Rd Unit 705, Sarasota, FL 34242

  Welcome to your beachfront oasis! Discover your perfect getaway in this beautifully refreshed 7th-floor condo, offering stunning balcony views of the Gulf of Mexico. With 1,285 square feet of living space, this fully furnished property features 2 bedrooms and 2 full bathrooms—all you need to bring is your bathing suit and toothbrush! The light-filled great room seamlessly connects the kitchen,

  Beverly Schroeder PLUMLEE GULF BEACH REALTY

  5830 Midnight Pass Rd Unit 705, Sarasota, FL 34242
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  /26

  $4,900 per month

  • 1 Bed
  • 1 Bath
  • 698 Sq Ft
  • Condo for Rent

  5400 Ocean Blvd Unit 1-5, Sarasota, FL 34242

  AVAILABLE for 2026 season. Turnkey furnished unit in the exclusive Terrace building on Siesta Key beach steps away from Siesta Key Village. Enjoy a swim from the elevated pool and catch a sunset while relaxing with a drink. This first floor condo offers a very large balcony with partial beach views as well as Siesta Village and is on the same floor to access the pool area. Washer and dryer are

  Brenda Cozy COLDWELL BANKER REALTY

  5400 Ocean Blvd Unit 1-5, Sarasota, FL 34242
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  /2

  $1,300,000 Sold Jun 11, 2025

  329 Avenida Leona, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1972

  Last Sold Summary

  • 20% Below List Price
  • $781/SF
  • 81 Days On Market

  Current Estimated Value $1,233,996

  Last Listing Agent Randy Owens COLDWELL BANKER REALTY

  329 Avenida Leona, Sarasota, FL 34242
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  /27

  Est $568,348 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft

  1600 Cove II Place Unit 414, Sarasota, FL 34242

  1600 Cove II Place Unit 414, Sarasota, FL 34242
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  /35

  $759,000

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft

  1328 Siesta Bayside Dr Unit 1328C, Sarasota, FL 34242

  Welcome to Gulf & Bay Club Bayside, one of Siesta Key’s most desirable resort-style communities. This turnkey-furnished residence offers the perfect blend of coastal comfort, modern updates, and access to Siesta Key’s world-famous beaches. Designed with a bright, open layout and porcelain tile flooring throughout, the interior feels fresh and inviting from the moment you step inside. Oversized

  Roger Pettingell COLDWELL BANKER REALTY

  1328 Siesta Bayside Dr Unit 1328C, Sarasota, FL 34242
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  /30

  $3,500 per month

  • 2 Beds
  • 2 Baths
  • 991 Sq Ft
  • Condo for Rent

  1215 S Portofino Dr Unit 308, Sarasota, FL 34242

  BEAUTIFUL WATERFRONT CONDO IN SIESTA HARBOR! CANAL VIEWS • BEACH ACCESS • BOAT SLIPS ON SITE REASONABLY PRICE, CHECK AVAILABILITY. Condo available Fall 2025 — and May through December 2026! Step into coastal luxury in this private, beautifully furnished corner end-unit in the highly sought-after Dolphin Building of Siesta Harbor. Enjoy gorgeous water views of the canal from your enclosed

  Rosie DiPasquale JUDITH GUZZI & ASSOCIATES LLC

  1215 S Portofino Dr Unit 308, Sarasota, FL 34242
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  /2

  $640,000 Sold Dec 08, 2025

  141 Avenida Messina Unit 4, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,035 Sq Ft
  • Built 1966

  Last Sold Summary

  • 8% Below List Price
  • $618/SF
  • 60 Days On Market

  Last Listing Agent Joe Cleary RE/MAX ALLIANCE GROUP

  141 Avenida Messina Unit 4, Sarasota, FL 34242
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  /30

  Est $543,834 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 872 Sq Ft

  5968 Midnight Pass Rd Unit 157, Sarasota, FL 34242

  5968 Midnight Pass Rd Unit 157, Sarasota, FL 34242
• 

  /2

  $3,400,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,200 Sq Ft

  4185 Roberts Point Lot 18 Cir, Sarasota, FL 34242

  Pre-Construction. To be built. Brought to you by Noah Thomas Builders — where modern luxury meets timeless coastal elegance. A masterclass in luxury homebuilding, this Noah Thomas Builders contemporary coastal home offers an exceptional blend of modern aesthetics and is built to FEMA's latest standards. Step inside this 3240 sqft home offering four bedrooms, four bathrooms, an open-concept floor

  Holly Wikfors 1ST CLASS REAL ESTATE SUNCOAST

  4185 Roberts Point Lot 18 Cir, Sarasota, FL 34242
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  /17

  $15,000 per month

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft
  • House for Rent

  339 Avenida de Paradisio, Sarasota, FL 34242

  scape to luxury in our serene Sarasota home! ????Relax in your private oasis with a sparkling pool, hot tub, and expansive backyard. Enjoy the open-concept living area and three cozy bedrooms designed for ultimate comfort.??? Just a 3-Min Drive to Siesta Beach??? 10 Minutes to Crescent Beach????? 13-Min Walk to a Local BeachDiscover the best of Sarasota with us!

  Valerie McInerney LPT REALTY, LLC

  339 Avenida de Paradisio, Sarasota, FL 34242
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  /2

  $1,375,000 Sold May 09, 2025

  702 Treasure Boat Way, Sarasota, FL 34242

  • 4 Beds
  • 2.5 Baths
  • 2,299 Sq Ft
  • Built 2007

  Last Sold Summary

  • 14% Below List Price
  • $598/SF
  • 193 Days On Market

  Current Estimated Value $1,297,357

  Last Listing Agent Mark Borg MARKANGEL REALTY

  702 Treasure Boat Way, Sarasota, FL 34242
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  /53

  Est $602,811 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 975 Sq Ft

  1042 W Peppertree Ln Unit 119B, Sarasota, FL 34242

  1042 W Peppertree Ln Unit 119B, Sarasota, FL 34242
• 

  

  /55

  $670,000

  • 2 Beds
  • 2 Baths
  • 1,271 Sq Ft

  101 Whispering Sands Dr Unit 307, Sarasota, FL 34242

  Experience the pinnacle of coastal luxury in this completely updated, FULLY FURNISHED end-unit condo located in the relaxing community of Whispering Sands on Siesta Key. Overlooking a tranquil lagoon and offering private beachfront access, this 2-bedroom, 2-bath residence seamlessly blends modern comfort with serene island living. This rare end-unit offers extra privacy and natural light, along

  Todd Goodman KELLER WILLIAMS ON THE WATER S

  101 Whispering Sands Dr Unit 307, Sarasota, FL 34242
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  /36

  $2,300 per month

  • 1 Bed
  • 2 Baths
  • 780 Sq Ft
  • Condo for Rent

  1350 N Portofino Dr Unit 207, Sarasota, FL 34242

  This stunning one-bedroom, two-bathroom condo in Siesta Harbor in the Tarpon Building is the perfect combination of luxury, convenience, and breathtaking views. Located in a prime location, boating access, canal frontage, and mesmerizing Intracoastal Waterway views. Step inside and be captivated by the modern elegance of this home. The kitchen is a chef's dream, featuring stainless steel

  Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

  1350 N Portofino Dr Unit 207, Sarasota, FL 34242
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  /2

  $1,630,000 Sold Apr 28, 2025

  320 Avenida Leona, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 1,782 Sq Ft
  • Built 1964

  Last Sold Summary

  • 12% Below List Price
  • $915/SF
  • 47 Days On Market

  Current Estimated Value $1,435,176

  Last Listing Agent Ryan Vlasic COLDWELL BANKER REALTY

  320 Avenida Leona, Sarasota, FL 34242
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  /36

  Est $710,161 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,270 Sq Ft

  5961 Midnight Pass Rd Unit 303, Sarasota, FL 34242

  5961 Midnight Pass Rd Unit 303, Sarasota, FL 34242
• 

  

  /69

  $1,000,000

  • 4 Beds
  • 2 Baths
  • 1,859 Sq Ft

  630 Venice Ln, Sarasota, FL 34242

  One or more photo(s) has been virtually staged. Nestled near the gentle waters of Roberts Bay, this enchanting Siesta Key home rests on a quiet cul de sac street where the only sounds are the whisper of palms and the laughter of neighbors walking by. T location captures the essence of island life — peaceful, private, and just moments from where the sun dips into the Gulf. A short stroll or quick

  Rudy Dudon MICHAEL SAUNDERS & COMPANY

  630 Venice Ln, Sarasota, FL 34242
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  /40

  $11,000 per month

  • 3 Beds
  • 2 Baths
  • 1,495 Sq Ft
  • Condo for Rent

  1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242

  Gulf & Bay Club Bayside offers resort-style amenities, including two heated pools, tennis courts, and lush landscapes. With easy access to Siesta Key's renowned beaches, this condo epitomizes the pinnacle of coastal living, where luxury, comfort, and stunning bay vistas converge to create an unparalleled living experience.Guest reservations include beach tags, giving you private beach

  Andy Moore GULF COAST REALTY & MANAGEMENT

  1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242
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  /2

  $850,000 Sold Feb 26, 2025

  4431 Ocean Blvd, Sarasota, FL 34242

  • 3 Beds
  • 2 Baths
  • 2,832 Sq Ft
  • Built 1952

  Last Sold Summary

  • 38% Below List Price
  • $300/SF
  • 34 Days On Market

  Current Estimated Value $912,248

  Last Listing Agent Shawn Judy FLORIDA SUN & SAND REALTY

  4431 Ocean Blvd, Sarasota, FL 34242
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  /49

  Est $648,416 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 975 Sq Ft

  1140 W Peppertree Ln Unit 114, Sarasota, FL 34242

  1140 W Peppertree Ln Unit 114, Sarasota, FL 34242
• 

  

  /40

  $690,000 Open Sun 11AM - 1PM

  • 1 Bed
  • 1 Bath
  • 522 Sq Ft

  5400 Ocean Blvd Unit 8-05, Sarasota, FL 34242

  BEACH TERRACE - STUDIO GULF-FRONT RESIDENCE: YOUR PERFECT SIESTA KEY PIED-À-TERRE Discover your ideal coastal escape at Beach Terrace, perfectly positioned at the end of Siesta Key Village with direct Gulf of Mexico frontage. This charming studio residence offers the perfect pied-à-terre for those seeking an effortless weekend getaway to paradise. Whether you call Sarasota or Lakewood Ranch home,

  Mickey Kiernan MICHAEL SAUNDERS & COMPANY

  5400 Ocean Blvd Unit 8-05, Sarasota, FL 34242
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  /80

  $8,500 per month

  • 3 Beds
  • 2 Baths
  • 1,290 Sq Ft
  • House for Rent

  5216 Calle de Costa Rica, Sarasota, FL 34242

  Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Imagine a place where the warm sunshine beckons you to relax, unwind, and truly escape the everyday. Welcome to House of the Sun, a delightful 3-bedroom, 2-bathroom island bungalow meticulously designed for your ultimate Siesta Key retreat, perfectly located just a leisurely

  Beth Dilley ASCENDIA REAL ESTATE

  5216 Calle de Costa Rica, Sarasota, FL 34242
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  /2

  $599,000 Sold Nov 14, 2025

  5911 Midnight Pass Rd Unit 504, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 1,447 Sq Ft
  • Built 1984

  Last Sold Summary

  • 20% Below List Price
  • $414/SF
  • 314 Days On Market

  Last Listing Agent Katie Cintron COLDWELL BANKER REALTY

  5911 Midnight Pass Rd Unit 504, Sarasota, FL 34242
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  /41

  Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,463 Sq Ft

  5400 Ocean Blvd Unit 14-2 & 14-3, Sarasota, FL 34242

  5400 Ocean Blvd Unit 14-2 & 14-3, Sarasota, FL 34242
• 

  

  /26

  $834,900

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft

  6236 Midnight Pass Rd Unit 305, Sarasota, FL 34242

  Welcome to Siesta Dunes, where living the Siesta Key lifestyle comes naturally. Enjoy true beachside convenience with direct access to powdery white sand and the sparkling Gulf- no streets to cross, just a short, breezy walk to the beach, pool, or tennis courts right within the community. Whether you're strolling to dinner, biking to the Village, or simply putting your toes in the sand, every

  Alex Chau COLDWELL BANKER REALTY

  6236 Midnight Pass Rd Unit 305, Sarasota, FL 34242
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  /58

  $8,000 per month

  • 3 Beds
  • 2 Baths
  • 2,002 Sq Ft
  • House for Rent

  5640 Cape Leyte Dr, Sarasota, FL 34242

  It's all about the beach and the bourbon! This 1964 Siesta Key classic beach house with terrazzo flooring has been totally updated! So you and your family or friends can enjoy the 3 bedroom and 2 bathroom singly family home. The open floor plan makes plenty of space to cook in the fully equipped kitchen and hang in the living room or the enclosed lanai overlooking the pool! Take a stroll to the

  Beth Dilley ASCENDIA REAL ESTATE

  5640 Cape Leyte Dr, Sarasota, FL 34242
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  /2

  $455,000 Sold Aug 08, 2025

  1250 N Portofino Dr Unit 201, Sarasota, FL 34242

  • 2 Beds
  • 2 Baths
  • 991 Sq Ft
  • Built 1969

  Last Sold Summary

  • 27% Below List Price
  • $459/SF
  • 125 Days On Market

  Current Estimated Value $458,411

  Last Listing Agent Jessica Bow RE/MAX PALM

  1250 N Portofino Dr Unit 201, Sarasota, FL 34242
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  /38

  Est $614,230 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,271 Sq Ft

  199 Whispering Sands Dr Unit 204WAT, Sarasota, FL 34242

  199 Whispering Sands Dr Unit 204WAT, Sarasota, FL 34242

Showing Results 201 - 240, Page 6 of 18